- Biomimetic synthesis of galantamine: Via laccase/TEMPO mediated oxidative coupling
-
Laccase-mediated intramolecular oxidative radical coupling of N-formyl-2-bromo-O-methylnorbelladine afforded a novel and isolable spirocyclohexadienonic intermediate of galantamine. High yield and conversion of substrate were obtained in the presence of the redox mediator 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO). This laccase procedure, with an overall yield of 34%, represents a scalable and environmentally friendly alternative to previously reported syntheses of galantamine based on the use of potassium ferricyanide as an unspecific radical coupling reagent.
- Baratto, Maria Camilla,Bizzarri, Bruno Mattia,Botta, Lorenzo,Pogni, Rebecca,Saladino, Raffaele,Zippilli, Claudio
-
-
Read Online
- Facile synthesis of (±)-, (+)-, and (-)-galanthamine
-
The Amarylidacea alkaloid galanthamine (1a) is an acetylcholinesterase inhibitor that has been evaluated as a potential agent for the treatment of Alzheimer's disease. We report a very efficent synthesis of (±)-galanthamine [(±)-1a] from readily available
- Szewczyk,Wilson,Lewin,Carroll
-
-
Read Online
- Processes for the preparation of derivatives of 4a, 5, 9, 10, 11, 12-hexahydro-6H-benzofuro-[3a, 3, 2-ef][2]benzazepine
-
The invention relates to processes for the preparation of 4a,5,9,10,11,12-hexahydro-6H-benzofuro[3a,3,2-ef][2]benzazepine, or derivatives thereof. Furthermore, the invention also relates to the compounds formed during the preparation of 4a, 5,9,10,11,12-hexahydro-6H-benzofuro[3a,3,2-ef][2]benzazepine.
- -
-
-
- Processes for the preparation of derivatives of 4a,5,9,10,11,12-hexahydro-6H-benzofuro-[3a,3,2-ef][2]benzazepine
-
The invention relates to processes for the preparation of 4a,5,9,10,11,12-hexahydro-6H-benzofuro(3a,3,2-ef)(2)benzazepine, or derivatives thereof. Furthermore, the invention also relates to the compounds formed during the preparation of 4a,5,9,10,11,12-hexahydro-6H-benzofuro(3a,3,2-ef)(2)benzazepine.
- -
-
-
- New kilogram-synthesis of the anti-Alzheimer drug (-)-galanthamine
-
A concise, scalable synthesis of (-)-galanthamine, a drug being used for the treatment of Alzheimer's disease, is described. The yield of the critical phenolic coupling step was optimized to 45-50%. For the reduction of the aryl bromide, air-activated LiAlH4 was used and racemic narwedine was converted to (-)-narwedine by a second order asymmetric transformation.
- Czollner, Laszlo,Frantsits, Werner,Kueenburg, Bernhard,Hedenig, Ursula,Froehlich, Johannes,Jordis, Ulrich
-
p. 2087 - 2088
(2007/10/03)
-
- An improved synthesis of galanthamine
-
Modifications in the total synthesis of the Amarylidaceae alkaloid of galanthamine from commercially available isovanillin and tyramine have resulted in a shortened reaction sequence, which is amenable to upscaling and in improved product yield.
- Szewczyk,Lewin,Carroll
-
p. 1809 - 1811
(2007/10/02)
-